The reactivity of tetramesityldisilene with epoxides: dependence of product distributions on steric and structural characteristics of the epoxide

Abstract

Mono- and 1,1-disubstituted epoxides react with tetramesityldisilene ( 1) to give disilyl enol ethers ( 5) five-membered rings ( 6) and the products of epoxide deoxygenation, alkenes and 1,1,2,2-tetramesityl-3-oxa-1,2-disilacyclopropane ( 4). Adducts 5 and 6 are formed with complete regioselectivity, suggesting involvement of an epoxide ring-opened intermediate. Product ratios vary systematically with a dependence on the steric properties of the epoxide. Single crystal X-ray diffraction results are given for 6a and 6g, the five-membered ring products derived from propylene and cyclohexene oxides.